(5S,5aS,8aR,9R)-5-(tert-Butyl-dimethyl-silanyloxy)-9-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one | 642409-84-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: (5S,5aS,8aR,9R)-5-(tert-Butyl-dimethyl-silanyloxy)-9-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one
• 英文别名: (5S,5aS,8aR,9R)-5-[tert-butyl(dimethyl)silyl]oxy-9-[4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethoxyphenyl]-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-6-one
• CAS: 642409-84-5
• 化学式: C₃₃H₄₈O₈Si₂
• 分子量: 628.91
• InChiKey: CAHOMWSDXUTPFY-GGRYPKIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.81
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (5S,5aS,8aR,9R)-5-(tert-Butyl-dimethyl-silanyloxy)-9-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin
  参考文献：
  名称：

  Synthesis and antiproliferative activity of retroetoposide

  摘要：

  Retro-4'-demethyl-4-epipodophyllotoxin 6 was synthesized in eight steps and 10% overall yield from 4'-demethyl-4-epipodophyllotoxin 12. Subsequent coupling of 22 with 1-O-trimethylsilyl-4,6-O-ethylidene-beta-D-glucoside 26 afforded retroetoposide 5 which is 10-fold less cytotoxic than etoposide against L1210 cell line. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.044
• 作为产物：
  描述：

  4'-去甲基表鬼臼毒素 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium chlorite 、 lithium aluminium tetrahydride 、 氨基磺酸 、 三乙基硼氢化锂 、 戴斯-马丁氧化剂 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 6.0h， 生成 (5S,5aS,8aR,9R)-5-(tert-Butyl-dimethyl-silanyloxy)-9-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one
  参考文献：
  名称：

  Synthesis and antiproliferative activity of retroetoposide

  摘要：

  Retro-4'-demethyl-4-epipodophyllotoxin 6 was synthesized in eight steps and 10% overall yield from 4'-demethyl-4-epipodophyllotoxin 12. Subsequent coupling of 22 with 1-O-trimethylsilyl-4,6-O-ethylidene-beta-D-glucoside 26 afforded retroetoposide 5 which is 10-fold less cytotoxic than etoposide against L1210 cell line. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.044

文献信息

• Synthesis and antiproliferative activity of retroetoposide
  作者：Philippe Meresse、Prokopios Magiatis、Emmanuel Bertounesque、Claude Monneret

  DOI：10.1016/j.bmcl.2003.08.044

  日期：2003.11

  Retro-4'-demethyl-4-epipodophyllotoxin 6 was synthesized in eight steps and 10% overall yield from 4'-demethyl-4-epipodophyllotoxin 12. Subsequent coupling of 22 with 1-O-trimethylsilyl-4,6-O-ethylidene-beta-D-glucoside 26 afforded retroetoposide 5 which is 10-fold less cytotoxic than etoposide against L1210 cell line. (C) 2003 Elsevier Ltd. All rights reserved.